US4675391A - Glycoside derivatives - Google Patents

Glycoside derivatives Download PDF

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Publication number
US4675391A
US4675391A US06/832,374 US83237486A US4675391A US 4675391 A US4675391 A US 4675391A US 83237486 A US83237486 A US 83237486A US 4675391 A US4675391 A US 4675391A
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US
United States
Prior art keywords
compound
sub
sup
carboxyl group
compounds
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Expired - Fee Related
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US06/832,374
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English (en)
Inventor
Shohei Shibayama
Yuzi Matsuzaki
Shoji Yoshimura
Masayoshi Ito
Yoshiyasu Shitori
Tomoya Ogawa
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KANTO ISHI PHARMACEUTICAL CO Ltd
Kanto Ishiseiyaku Co Ltd
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Kanto Ishiseiyaku Co Ltd
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Assigned to KANTO ISHI PHARMACEUTICAL CO., LTD. reassignment KANTO ISHI PHARMACEUTICAL CO., LTD. ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: ITO, MASAYOSHI, MATSUZAKI, YUZI, OGAWA, TOMOYA, SHIBAYAMA, SHOHEI, SHITORI, YOSHIYASU, YOSHIMURA, SHOJI
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H3/00—Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
    • C07H3/06—Oligosaccharides, i.e. having three to five saccharide radicals attached to each other by glycosidic linkages
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/26—Acyclic or carbocyclic radicals, substituted by hetero rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H9/00—Compounds containing a hetero ring sharing at least two hetero atoms with a saccharide radical
    • C07H9/06—Compounds containing a hetero ring sharing at least two hetero atoms with a saccharide radical the hetero ring containing nitrogen as ring hetero atoms

Definitions

  • N-substituted neuraminic acid such as N-acetylneuraminic acids and the like are present in many animals and on the cell surface of several bacterias as a complex of sialic acid such as glycoprotein, glycolipid, oligosaccharide or polysaccharide.
  • N-substituted neuraminic acids have become important substances in medicine and pharmaceutics relative to nerve function, cancer, inflammation, immunity, viral infection, differentiation, hormone receptor etc and have been noted as unique active molecules located on the cell surface.
  • the role of N-substituted neuraminic acids in the complex of sialic acid has not been ascertained yet.
  • the inventors of the present invention have paid special attention to sialic acid which is a bio-inherent ingredient and they continued their research on control agents for immunity having few side effects because of its chemical modification and control effects for immunological surveillance.
  • the inventors have succeeded in finding the novel compounds of the present invention having immunoregulative effect in which suppressor T cell is activated and production of immunoglobulin of B cell is restrained.
  • the principal object of the present claimed invention is to provide novel compounds having an excellent immunological activity, especially the immunoregulation effect.
  • Another object of this invention is to provide effective processes for preparing the novel compounds.
  • novel glycoside having the following general formula (I) are provided.
  • R 1 is selected from ##STR3## group, alkoxycarbonyl group, carboxyl group and salts of carboxyl group
  • R 2 is alkoxycarbonyl group, carboxyl group or salts of carboxyl group when R 1 is ##STR4## group
  • R 2 is ##STR5## group when R 1 is alkoxycarbonyl group, carboxyl group or salt of carboxyl group
  • R 3 is a hydrogen atom or acetyl group.
  • the alkoxycarbonyl group of the present invention may be exemplified by methoxycarbonyl group, ethoxycarbonyl group or the like.
  • the salt of carboxyl group may be exemplified by alkali metal salt or alkali earth metal salt such as sodium salt, potasium salt, calcium salt and the like, of carboxyl group.
  • the compound (I) of the present invention includes a ⁇ configuration derivative ( ⁇ -derivative) of which R 1 is ##STR6## group and a ⁇ configuration derivative ( ⁇ -derivative) of which R 2 is ##STR7## group.
  • the compound of the present invention represented by the general formula (I) can be prepared by a method shown by the following serial formulas from methyl-2-chloro-4,7,8,9-tetra-0-acetyl- ⁇ -D-N-acetylneuraminate (hereinafter compound (II)) and 5-fluoro-1-[(2-hydroxyethoxy)methyl]uracil (hereinafter compound (III)) and obtained as compounds (IV) to (XI).
  • the compounds (IV) to (XI) were named as follows:
  • compound (X) 1-0-[(5-N-acetyl-3,5-dideoxy- ⁇ -D-glycero-D-galacto-2 nonulopyranosyl)onic acid]-2-0-[(2,4-dioxo-5-fluoro-1,2,3,4-tetrahydropyrimidin-1-yl)methyl]-ethane diol
  • reaction carried out in the presence of CF 3 SO 3 Ag may preferably be carried out in a solvent such as tetrahydrofuran, acetonitrile, methylene chloride or the like at temperatures of room temperature to -50° C. for about 5 to 60 minutes.
  • a solvent such as tetrahydrofuran, acetonitrile, methylene chloride or the like
  • the reaction time be about 20 minutes and the solvent be tetrahydrofuran.
  • novel compound (VI) ( ⁇ -derivative) can be obtained by transesterification of the compound (IV) using sodium methoxyde in methanol.
  • novel compound (VII) ( ⁇ -derivative) of the present invention can be obtained from the compound (V).
  • the compounds having the formula (I) have an excellent activity capable of adjusting the strength of the immune system.
  • Activity capable of adjusting the strength of the immune system could be ascertained by the following method.
  • N-substituted neuraminic acid derivatives of the present invention which were indicated in the activation of T-cell in the previous experiment, the function against the production of immunoglobulin was studied further by measuring the number of plaque-forming cells (PFC).
  • N-substituted neuraminic acid derivatives of the present invention having activation function to suppressor T cell are expected to be effective in clinical applications as an agent for adjusting the strength of the immune system.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Immunology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Saccharide Compounds (AREA)
US06/832,374 1985-03-06 1986-02-24 Glycoside derivatives Expired - Fee Related US4675391A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP60-43970 1985-03-06
JP60043970A JPS61204190A (ja) 1985-03-06 1985-03-06 グリコシド及びその製造方法

Publications (1)

Publication Number Publication Date
US4675391A true US4675391A (en) 1987-06-23

Family

ID=12678563

Family Applications (1)

Application Number Title Priority Date Filing Date
US06/832,374 Expired - Fee Related US4675391A (en) 1985-03-06 1986-02-24 Glycoside derivatives

Country Status (12)

Country Link
US (1) US4675391A (xx)
EP (1) EP0194563A3 (xx)
JP (1) JPS61204190A (xx)
KR (1) KR880000704B1 (xx)
CN (1) CN1018646B (xx)
AU (1) AU561320B2 (xx)
ES (1) ES8704180A1 (xx)
FI (1) FI79543C (xx)
HU (1) HU195228B (xx)
MC (1) MC1740A1 (xx)
NO (1) NO164660C (xx)
ZA (1) ZA861619B (xx)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4774327A (en) * 1985-10-11 1988-09-27 Mect Corporation N-glycolylneuraminic acid derivative
US4774326A (en) * 1985-10-11 1988-09-27 Mect Corporation Process for preparing N-glycolylneuraminic acid derivatives
US5015631A (en) * 1987-06-25 1991-05-14 Mect Corporation Repairing agent for cells and tissues
WO1991009975A1 (en) * 1989-12-29 1991-07-11 Symex Corp. Chromogenic 7- or 8-position modified n-acetylneuraminic acid substrates and methods for diagnosing human influenza therewith
US20030228981A1 (en) * 2002-03-26 2003-12-11 Georgia-Pacific Resins, Inc. Slow release nitrogen seed coat

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4248999A (en) * 1976-10-28 1981-02-03 Sankyo Company Limited 5-Fluorouracil derivatives and process for preparing thereof
JPS60181295A (ja) * 1984-02-27 1985-09-14 Pentel Kk 酸化皮膜を有するアルミニウムまたはアルミニウム合金基体の製造方法

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5738774A (en) * 1980-08-19 1982-03-03 Chugai Pharmaceut Co Ltd Uracil derivative and its preparation
DE3474632D1 (en) * 1983-03-01 1988-11-24 Crc Ricerca Chim Pharmaceutical compositions containing the cytidine monophosphate of 5-acetamido-3,5-dideoxy-d-glycero-d-galactononulosaminic acid

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4248999A (en) * 1976-10-28 1981-02-03 Sankyo Company Limited 5-Fluorouracil derivatives and process for preparing thereof
JPS60181295A (ja) * 1984-02-27 1985-09-14 Pentel Kk 酸化皮膜を有するアルミニウムまたはアルミニウム合金基体の製造方法

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
Can J. Chem.: 60, 547 553 (1982). *
Can J. Chem.: 60, 547-553 (1982).
Chem. Bor.: 99, 611 617 (1966). *
Chem. Bor.: 99, 611-617 (1966).

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4774327A (en) * 1985-10-11 1988-09-27 Mect Corporation N-glycolylneuraminic acid derivative
US4774326A (en) * 1985-10-11 1988-09-27 Mect Corporation Process for preparing N-glycolylneuraminic acid derivatives
US5015631A (en) * 1987-06-25 1991-05-14 Mect Corporation Repairing agent for cells and tissues
WO1991009975A1 (en) * 1989-12-29 1991-07-11 Symex Corp. Chromogenic 7- or 8-position modified n-acetylneuraminic acid substrates and methods for diagnosing human influenza therewith
US20030228981A1 (en) * 2002-03-26 2003-12-11 Georgia-Pacific Resins, Inc. Slow release nitrogen seed coat

Also Published As

Publication number Publication date
NO164660C (no) 1990-10-31
EP0194563A2 (en) 1986-09-17
NO860837L (xx) 1986-09-08
FI79543B (fi) 1989-09-29
ZA861619B (en) 1986-11-26
JPH0560474B2 (xx) 1993-09-02
FI860930A0 (fi) 1986-03-05
CN1018646B (zh) 1992-10-14
HU195228B (en) 1988-04-28
EP0194563A3 (en) 1988-06-01
JPS61204190A (ja) 1986-09-10
MC1740A1 (fr) 1987-02-26
ES552676A0 (es) 1987-03-16
HUT42501A (en) 1987-07-28
KR860007276A (ko) 1986-10-10
FI79543C (fi) 1990-01-10
KR880000704B1 (ko) 1988-04-25
AU5411686A (en) 1986-09-11
FI860930A (fi) 1986-09-07
CN86102125A (zh) 1987-01-07
AU561320B2 (en) 1987-05-07
ES8704180A1 (es) 1987-03-16
NO164660B (no) 1990-07-23

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Owner name: KANTO ISHI PHARMACEUTICAL CO., LTD., NO. 1-1, NISH

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